Synthesis and anti-HCV determinant motif identification in pyranone carboxamide scaffold

Balaraju, Tuniki; Konreddy, Ananda Kumar; Parveen, Afsana; Toyama, Massaki; Ito, Wataru; Karampuri, Srinivas; Baba, Masanori; Sharon, Ashoke; Bal, Chandralata

doi:10.1016/j.bmcl.2015.09.060

Cited by 6 publications

(2 citation statements)

References 16 publications

(15 reference statements)

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“…2H-pyran-2-one moiety, a cyclic lactone shows its significant presence in natural products and are essential building blocks in synthetic organic and medicinal chemistry [13][14][15][16][17][18]. Owing to their profound biological activities, we focused our research interest on pyranones and their transformation into potential biologically active scaffolds [19][20][21]. In this present work, we identified a microwave-assisted hydrodecarboxylation process for 2Hpyran-3-carboxylic acids under mild conditions.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐assisted decarboxylation of 2H‐Pyran‐3‐carboxylic acid derivatives under basic condition

Mishra

Bal

2022

Journal of Heterocyclic Chem

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Despite the availability of several methods for decarboxylation, this area remains exploratory and requires new development. Here, we report a highly efficient microwave‐assisted hydrodecarboxylation of 4‐(methylthio)‐2‐oxo‐6‐aryl‐2H‐pyran‐3‐carboxylic acids (1a‐k) under basic condition to obtain 4‐(methylthio)‐6‐aryl‐2H‐pyran‐2‐ones (2a‐k) with >90% yield. The requirement of proton source from the solvent was observed by performing the reactions of 1b and 1e in CD3OD to obtain deuterated compounds 2 l and 2 m respectively. All compounds were characterized by spectroscopic analysis. Further, compounds 2b and 2e were analyzed by single‐crystal X‐ray diffraction studies.

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Section: Introductionmentioning

confidence: 99%

Microwave‐assisted decarboxylation of 2H‐Pyran‐3‐carboxylic acid derivatives under basic condition

Mishra

Bal

2022

Journal of Heterocyclic Chem

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“…Some pyrazole compounds have been developed as commercial drugs and pesticides, such as tebufenpyral, fipronil, fenpyroximate, tolfenpyrad, and chlorantraniliprole. In addition, carboxamide is a key substructure in many compounds, which displayed various biological activities, such as antifungal, herbicidal, insecticidal , antiproliferative , PDE4 inhibitors, and anti‐hepatitis C virus . Many carboxamide fungicides had been developed by BASF, Bayer, Syngenta, Monsanto, Sumitomo Chemical, and so on.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Nematocidal Activity of N‐Substituted 3‐Methyl‐1H‐pyrazole‐4‐carboxamide Derivatives Against Meloidogyne incognita

Shen

et al. 2018

Journal of Heterocyclic Chem

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A series of novel pyrazole carboxamides were designed and synthesized through multi‐step reactions from ethyl acetoacetate and triethyl orthoformate, and their structures were characterized by Fourier transform infrared, 1H‐NMR, 13C‐NMR, mass spectrometry, and elemental analysis. The preliminary insecticidal activity showed that some of them possessed good insecticidal activities against Meloidogyne incognita.

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Base Catalyzed Scaffold Shift from Pyranone Carboxamide to Pyrazolyl Acetamide through Intramolecular Ring Transformation

Rozy

Sharon

2019

ChemistrySelect

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Scaffold shift of biologically active pyranone carboxamide to pyrazolyl acetamide, which is another biologically important scaffold was achieved through one‐pot base catalyzed metal‐free intramolecular ring transformation. Out of the two probable mechanistic pathways (Figure 3), substitution at C‐4 by hydrazineyl leading to a pyranone intermediate followed by an intramolecular attack of hydrazineyl at C‐6 and decarboxylation to yield pyrazolyl acetamides was rationalized through LCMS, UV monitoring and computational studies.

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Synthesis and anti-HCV determinant motif identification in pyranone carboxamide scaffold

Cited by 6 publications

References 16 publications

Microwave‐assisted decarboxylation of 2H‐Pyran‐3‐carboxylic acid derivatives under basic condition

Microwave‐assisted decarboxylation of 2H‐Pyran‐3‐carboxylic acid derivatives under basic condition

Synthesis and Nematocidal Activity of N‐Substituted 3‐Methyl‐1H‐pyrazole‐4‐carboxamide Derivatives Against Meloidogyne incognita

Base Catalyzed Scaffold Shift from Pyranone Carboxamide to Pyrazolyl Acetamide through Intramolecular Ring Transformation

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